Ethyl bromodifluoroacetate

Ethyl bromodifluoroacetate is an ester with the chemical formula F₂BrCH−CO₂CH₂CH₃. It can be used to introduce the CF₂ group when synthesising chemical compounds. It is a colorless to yellow liquid. It is an ethyl ester of bromodifluoroacetic acid.

Ethyl bromodifluoroacetate

Names
IUPAC name Ethyl 2-bromo-2,2-difluoroacetate
Systematic IUPAC name Ethyl 2,2-dibromo-2-fluoro-acetate
Other names Difluorobromoacetic acid ethyl ester
Identifiers
CAS Number	667-27-6 Y
3D model (JSmol)	Interactive image
ChemSpider	62789
ECHA InfoCard	100.010.517
EC Number	211-567-0
PubChem CID	69585
UNII	2QFZ6JJ5YH Y
CompTox Dashboard (EPA)	DTXSID40216845
InChI InChI=1S/C4H5BrF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3 Key: IRSJDVYTJUCXRV-UHFFFAOYSA-N InChI=1/C4H5Br2FO2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
SMILES BrC(Br)(F)C(=O)OCC
Properties
Chemical formula	F2BrCHCO2CH2CH3
Molar mass	202.983 g·mol−1
Appearance	Colorless to slightly yellow liquid
Density	1.583 g/mL
Boiling point	82 °C (180 °F; 355 K) pressure is at 33 torr
Vapor pressure	1.36 mmHg at 25°C
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H314
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Formation

Ethyl fluorosulfonoxydifluoroacetate can react with sodium bromide (NaBr) to produce ethyl bromodifluoroacetate. And this reaction could happen in the solvent sulfolane. The reactions takes 12 hours at 100 °C with a yield of 31%.

Reactions

Ethyl bromodifluoroacetate, and other similar compounds containing a CF₂ units can be generated using the Reformatsky reagent with aldehydes and ketones. This yields 2,2-difluoro-3-hydroxy esters. Also ethyl bromdifluoroacetate is considered to be a good compound in generation of compounds and for testing with other organic compounds like lactones, imines and other amino acids.